N-[3-[6-[4-[(2R)-1,4-Dimethyl-3-oxopiperazin-2-yl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide → N-[3-(6-{4-[(2S)-1,4-Dimethyl-3-oxopiperazin-2-yl]anilino}-4-methyl-5-oxo-4,5-dihydropyrazin-2-yl)-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide

Participants

Reaction Steps

The racemic mixture (12) was subjected to chiral separation on Chiralcel-AD-H (60% isopropanol in heptane, with 0.1% trifluoroacetic acid) to give individual enantiomers at 4.6 minutes (20) ((−) isomer) ([α]D25=−37.8° (c=3.75, CHCl3), mp=181-183° C.) and at 9.2 minutes (19) ((+) isomer) ([α]D25=+38.8° (c=3.57, CHCl3), mp=180-182° C.). Alternatively, the racemic mixture (12) was subjected to chiral separation on Chiralpak AD (75% isopropanol in heptane, at 1 mL/min) and individual enantiomers were collected from 17 to 27 minutes (20) ((−) isomer) and from 27 to 60 minutes (19) ((+) isomer).

Provenance & Evidence